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|Title:||Base-catalysed solvolysis of acylsilanes||Authors:||Pietropaolo, D.
|Issue Date:||1980||Project:||None||Journal:||JOURNAL OF ORGANOMETALLIC CHEMISTRY||Abstract:||
Kinetic studies have been made of the hydrolysis of XC6H4COSiR3 compounds (R = Me, Et, Ph) in a mixture of THF (3 vol.) and aqueous sodium hydroxide (1 vol.). The rates of cleavage of p-NO2C6H4CH2SiMe3, C6H5COSiMe2C6H5 and C6H5COSiMe2C6H4Cl-p compounds under the same conditions have also been measured. Electron-attracting substituents on either side of the bond being broken lead to an increase in the rate. For the XC6H4COSiR3 compounds, the effects of the substituents X correlate excellently with their Hammett ╧â constants (╧▒ = 3.5 and 2.5 for R = Me and Ph, respectively). The data are consistent with a mechanism in which the attack of the hydroxide ion occurs at the carbonyl C atom
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